4-Methylmorpholine → HCID 59708628, compound

Participants

Reaction Steps

To a 25 mL recovery flask was added [3-(4-Trimethylsilanyl-[1,2,3]triazol-1-yl)-phenoxy]-acetic acid 6 (483 mg, 1.66 mmol, 1.0 eq.) and a stirbar. O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.26 g, 3.3 mmol, 2.0 eq.), DMF (8 mL), and N-methylmorpholine (503 μL, 4.98 mmol, 3.0 eq.) were added. The mixture was stirred at room temperature for 30 min. 5-amino-2-chlorobenzotrifluoride (649 mg, 3.3 mmol, 2.0 eq.) was added and the reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with a succession of 10% aq. LiCl (3×50 mL), H2O (50 mL), and sat'd aq. NaCl (50 mL). The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated to give a grayish solid. The solid was recrystallized in hot MeOH to give a light gray solid, which by LC/MS was a mixture of product and the corresponding de-silylated material (200 mg). The mixture was taken on to the next step without further purification. LC/MSD (HP Series 1100 MSD) MS (ES+) m/z 469.1 (M+H)+1

Provenance & Evidence